Bend your business toward your passion

Joshua Rogers is the CEO and Founder of Arete Wealth, a Nashville-based wealth management firm that provides high-net worth individuals and institutions access to alternative investment access, venture capital, and private equity.

I grew up in the suburbs of northern Virginia in a town called Sterling. It’s near Dulles Airport. My father is a retired captain in the Navy. My mom spent her entire career at the EPA. I attended Broad Run High School in Ashburn. Back then, people called it “Cornfield U.” because it was surrounded by farms. These days Ashburn is a booming and upscale part of Loudoun County.

I was a very serious junior tennis player. I ranked as high as 7th in the mid-Atlantic USTA junior leagues. I also played soccer, golf and baseball. But my real passion was debate. I was good. We competed against schools that were way larger and wealthier, traveling to Kentucky, Harvard and Kansas. One year, we lost in the semi-finals.

Our debate coach was named Ron Richards. He’s from Manassas, VA and wrote a book about his experiences coaching debate for 35 years. Our most famous debate team alumni is Patton Oswalt, the actor and comedian.

I had planned to go to college at Dartmouth, but at the last minute I met a sophomore at George Washington University and became so intoxicated with her that I applied to schools in the vicinity. I got into Johns Hopkins in Baltimore. I ended up marrying her later on.

My dad is a graduate of the U.S. Merchant Marine Academy who thinks the U.S. military is the greatest thing in human existence and the only acceptable education is going to a service academy. I wanted to pave my own path but compromised by doing Army ROTC and agreeing to major in bio-medical engineering. I hated both.

I started taking philosophy and art history classes but became disillusioned in a literary theory class when one of the teachers ripped apart Aristotle. I thought that wasn’t intellectually honest.

My parents stopped supporting me that summer so I worked as a barback at PJ’s Wings and an assistant in the Hopkins library stacking books. There was an advertisement on the corkboard for a student with a car. A retired philosophy professor named Kingsley Blake Price needed some help around his house as he was blind.

Meeting Kingsley changed my life. He lived in a beautiful townhome and was very into gardening. He said I should look at transferring to St. John’s College. “You have a hungry mind,” he told me. We drove to Annapolis to see the campus. There was a seminar class going on and it was amazing. Kingsley helped me transfer.

St. John’s played an enormous role in my life. I am currently the Secretary of the board and have been a trustee for 10 years.The school taught me that the first step towards wisdom was knowing what you don’t know. I have a tattoo written in ancient Greek of the famous saying from Plato’s Apology: “The unexamined life is not worth living.”

I graduated in 1998 and applied to be a Rhodes Scholar, but didn’t get it so I went to study law at Georgetown. At that point I got a call out of the blue with an offer to join a new business run by Jay Walker who was on the verge of founding Priceline.com.

I hated what I was doing and didn’t want to be a lawyer so when they offered me $60,000 in salary plus $10,000 to relocate, I moved to join Walker Digital in Stamford, Conn. They said we were going to get rich.

We were co-inventors on a suite of patents that became the basis for “name your price” e-commerce patents. We came up with a model for dynamic pricing using the Black Scholes options formula and later applied it to airline seats.

Jay was a big Trekkie. He had been to every convention and William Shatner knew him as a fan. Jay reached out and asked Shatner to do commercials for Priceline.com. He said “I can’t afford to pay you cash, but I can give you stock.”

The commercials took off like wildfire. We got a huge amount of traffic. Jay parlayed that into a big VC partnership and we went public in March of 1999 at $16 a share. The stock shot up to about $120 and then back down to $2. New management fired us.

I decided to try my hand at being a stockbroker. My wife was pregnant and I was feeling in a pinch to provide for our family. I got an offer from another St. John’s graduate to join a firm called Prime Chartered Limited brokerage. We cold called executives. I was very good at it, but I didn’t like the transactional aspect. I worried I wasn’t helping anyone.

"To be successful you need to develop and maintain relationships with other strong-willed, healthy-egoed people."

I started looking for other opportunities and answered an ad for American Express Financial Advisors in D.C. We moved to Rockville, Maryland and I started as a financial advisor. It wasn’t hard because Amex card members checked a box asking for an advisor to call them. I would drive to their homes, sit at the kitchen table and talk.

I became a district manager and worked my way up the ranks. In 2003, I moved to Chicago to become a regional manager. I’d never been to Chicago, but I loved it. It’s like New York but the people are friendlier and it’s cleaner. We had 2 children by then. When Amex spun off the business to Ameriprise Financial I didn’t want to move to Minneapolis.

So in 2007 I decided to start my own business. The idea was to provide endowment-style alternatives for the mass affluent – doctors and lawyers who earn $500,000 to $1,000,000. They were smart enough to know the smart money invests in a different way and they want to get exposure to venture capital and private equity.

I took out a 2nd mortgage against my house and cashed in my 401k. I put in everything I had to start the company. I bought a shell broker-dealer and renamed it Arete. It means excellence and virtue. I got the idea from reading Aristotle's Nicomachean Ethics at St. John’s.

One good piece of advice I got when I was younger was to “bend your business to your passions.” In my case that meant adding an element to Arete to advise clients on art as an investment.

I got into art as a kid. My grandfather was a docent at the National Gallery of Art in Washington and would take me there on the weekends. I always wanted to collect. When I started making some money I got involved in the contemporary art scene.

Arete has since partnered with Scott Lynn, the CEO and founder of Masterworks, to sell art as a security.

I’ve been running Arete for 15 years and my goal is to do so for another 15. My business is a people business. I didn’t invent a widget. To be successful you need to develop and maintain relationships with other strong-willed, healthy-egoed people. Everyone is battling for their self interest and more of a slice of the pie.

What’s working for me as a leader is radical authenticity and radical vulnerability. Really laying our cards on the table and encouraging people to understand how we can come to a win-win for both of us. It’s a long-term mentality.